Guest Post: What it’s Really Like to Date in New York City

I asked my friend to write a post on dating in NYC. She’s the only one I feel could really tackle the beast. Her stories over time have been wow-worthy, hopeful, irksome, sweet… basically all of the above. I wanted her to capture what it truly felt like to date here in this gigantic city, because being in a relationship for almost 10 years, I don’t knowshit. Here’s the brilliance of what she came up with.

By: My anonymous friend

I’ve lived in New York City for 10 years and when Mary asked me to write about “a typical date in NYC,” I laughed and walked away. In an ever-changing, incredibly diverse city of 8.5 million people, I can confidently state that there is no such thing as a typical date.

I’m a 20-something-year-old, college educated, heterosexual white girl. I can only speak to my own experiences. I have no idea what it’s like to date as a member of the LGBTQ+ community, as a person of color, while pregnant, over 40, religious, homeless, polyamorous, etc. But as I sat and reflected on my own adventures in the NYC dating scene, I could only help but wonder; is there such a thing as a typical date in a city as capricious as its’ bagel offerings? Clearly not. So instead of detailing the impossible, I will list of several of the many, many dates I’ve endured over the past 10 years.

A brief caveat: I haven’t been on a date in nearly 2 years, so I have no idea what it’s like to date in a post-Trumpian, post #MeToo world, but I can only imagine things haven’t changed much (though I hope that’s the case). I am now in an incredibly loving and exciting relationship with someone I met online (yes, it’s possible. They’re not all douchebags, it just takes a lot of time to find the good ones).

So without further ado, here is a brief list of the people I’ve dated:

The vet who spat on me throughout our entire conversation in which he detailed his parents’ messy divorce, his haunting PTSD, and how for exercise, he puts bricks in his backpack and walks around the city.

The photographer who I’d been seeing for three weeks who, on one of our “dates” did his taxes. One night he cooked me dinner (velveeta mac and cheese and microwaved vegetable… romantic) and said, “See you next week.” I never heard from him again.

The guy who took me out to play skeeball but made me hold his beer while he played darts by himself the whole night.

The vegan whose dream job was to “make t-shirts for stoners.”

The boring guy who forced me to sit through a near-endless dinner while he put ketchup on his fries individually (with one of those glass bottles) because he thought putting it on the side would ruin them.

The lawyer with the fancy apartment who told me he couldn’t use condoms because he “had a soccer accident” (points for creativity).

The guy who took me to the movies on our first date, refused my offer to pay, and then asked for my share of the tickets 10 minutes later.

The guy with the secret girlfriend.

The other guy with the secret girlfriend.

The guy who lived with his parents.

The comedian with a burgeoning mullet who tried to braid my hair.

The guy brought three friends and ignored me all night then got mad at me when he thought I was hitting it off with one of his friends (I wasn’t. I was just grateful someone was indulging me in conversation).

The musician who cheated on me.

The chef who tried to sext me at 10am on a Wednesday by asking “are you naked”? At 10am. On a Wednesday.

So best of luck out there- enjoy the experiences, as unsavory and weird as they are- if only for the stories they’ll give you for the rest of your life.

How’d she do? Write your own experiences in the comments below or find me on Instagram @maryinmanhattan.

Mary in Manhattan

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Heyooo - I’m Mary and I’m here to show you the real, liveable, New York City - the one you’ll be excited to share with your friends. See what’s truly AWESOME to eat and do in NYC, no matter what your budget. Plus, I’m always on the lookout for noteworthy things to do when I travel to other cities around the world. So get out of Times Square and discover something cool with me!
P.S. - all opinions are my own